C212
N-Acetyl-L-cysteine
Synonym(s):
LNAC, NAC
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About This Item
Linear Formula:
HSCH2CH(NHCOCH3)CO2H
CAS Number:
Molecular Weight:
163.19
EC Number:
210-498-3
UNSPSC Code:
12352200
PubChem Substance ID:
Beilstein/REAXYS Number:
1724426
MDL number:
InChI key
PWKSKIMOESPYIA-BYPYZUCNSA-N
InChI
1S/C5H9NO3S/c1-3(7)6-4(2-10)5(8)9/h4,10H,2H2,1H3,(H,6,7)(H,8,9)/t4-/m0/s1
SMILES string
CC(=O)N[C@@H](CS)C(O)=O
mp
106-108 °C (lit.)
storage temp.
−20°C
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Biochem/physiol Actions
Antioxidant and mucolytic agent. Increases cellular pools of free radical scavengers. Reported to prevent apoptosis in neuronal cells but induce apoptosis in smooth muscle cells. Inhibits HIV replication. May serve as a substrate for microsomal glutathione transferase.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2
Storage Class
13 - Non Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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Suzanne M Cloonan et al.
Journal of medicinal chemistry, 58(11), 4494-4505 (2015-05-12)
Ruthenium polypyridyl complexes show great promise as new photodynamic therapy (PDT) agents. However, a lack of detailed understanding of their mode of action in cells poses a challenge to their development. We have designed a new Ru(II) PDT candidate that
I-Ta Lee et al.
The American journal of pathology, 175(2), 519-532 (2009-07-18)
Oxidative stresses are believed to play an important role in the induction of both cell adhesion molecules and pro-inflammatory cytokines, a key event in a variety of inflammatory processes. The enzyme heme oxygenase-1 (HO-1) functions as an antioxidant and serves
Yuval Samuni et al.
Biochimica et biophysica acta, 1830(8), 4117-4129 (2013-04-27)
N-acetylcysteine (NAC) has been in clinical practice for several decades. It has been used as a mucolytic agent and for the treatment of numerous disorders including paracetamol intoxication, doxorubicin cardiotoxicity, ischemia-reperfusion cardiac injury, acute respiratory distress syndrome, bronchitis, chemotherapy-induced toxicity
Michael Berk et al.
Trends in pharmacological sciences, 34(3), 167-177 (2013-02-02)
N-Acetylcysteine (NAC) targets a diverse array of factors germane to the pathophysiology of multiple neuropsychiatric disorders including glutamatergic transmission, the antioxidant glutathione, neurotrophins, apoptosis, mitochondrial function, and inflammatory pathways. This review summarises the areas where the mechanisms of action of
Luigi Franchi et al.
Journal of immunology (Baltimore, Md. : 1950), 193(8), 4214-4222 (2014-09-17)
The nucleotide-binding oligomerization domain-like receptor pyrin domain-containing 3 (Nlrp3) inflammasome plays an important role in inflammation by controlling the maturation and secretion of the cytokines IL-1β and IL-18 in response to multiple stimuli including pore-forming toxins, particulate matter, and ATP.
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